A six-membered nitrogen-oxygen-silicon heterocyclic compound and its preparation method

A technology of heterocyclic compound and silicon oxynitride, which is applied in the field of six-membered silicon oxynitride heterocyclic compound and its preparation, can solve the problem of weak reducibility of hydrogen-containing silane, achieve short reaction time, good application prospects, and mild reaction conditions Effect

Active Publication Date: 2021-01-01
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Known hydrosilanes are weakly reducing, therefore, the reduction of unsaturated imines can only be achieved under the action of a catalyst

Method used

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  • A six-membered nitrogen-oxygen-silicon heterocyclic compound and its preparation method
  • A six-membered nitrogen-oxygen-silicon heterocyclic compound and its preparation method
  • A six-membered nitrogen-oxygen-silicon heterocyclic compound and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1) Preparation of 6-tert-butyl-2((phenylimino)-4-methylphenol

[0034] Under the protection of nitrogen, use 2mmol 2-tert-butyl-p-methyl-phenol and 2.2mmol paraformaldehyde to react in acetonitrile (100mL) at reflux (100℃~110℃) for 2 hours, cool to room temperature, add 5% Wash with hydrochloric acid, then extract with diethyl ether (3x100mL), collect the diethyl ether phase, then wash with saturated brine (100mL), and wash the organic phase with anhydrous MgSO 4 Dry and filter. Concentrated and recrystallized to obtain 2-tert-butyl-p-methyl-valylal with a yield of 95%.

[0035] 1 mmol of 2-tert-butyl-p-methyl-valylal and 1.2 mmol of 2,6-diisopropylaniline synthesized above were refluxed (90° C.) in absolute ethanol (50 mL) and reacted for 1 hour. Cool to room temperature and recrystallize from ethanol to obtain 6-tert-butyl-2(2,6-diisopropylbenimino)-4-methylphenol with a yield of 90%.

[0036]2) Preparation of 3,4-benzyl, 2-oxa, 6-aza, 1,1-dichlorosilane compounds ...

Embodiment 2

[0048] 1 mmol of 2-tert-butyl-p-methyl-glycanal and 1.2 mmol of aniline synthesized according to the route of Example 1 were refluxed (90° C.) in absolute ethanol (50 mL) and reacted for 1 hour. Cool to room temperature, recrystallize with ethanol to obtain 6-tert-butyl-2((phenylimino)-4-methylphenol, the yield is 90%, and set aside.

[0049] Under nitrogen protection, 50 mL of n-hexane was added to a dry Shrek bottle, and then 1.2 mmol of trichlorosilane was added to dissolve 1.0 mmol of 6-tert-butyl-2((phenylimino)- 4-Methylphenol and 1.1mmol of triethylamine were slowly added dropwise to the above system at 0°C, reacted for 1.5h, concentrated the solvent to 10mL, placed in a -20°C refrigerator for recrystallization, and obtained white crystal 3, 4-Benzene, 2-oxa, 6-aza, 1,1-dichlorosilane compounds, the yield is 95%, and the structural formula is as follows:

[0050]

Embodiment 3

[0054] 1 mmol of 2-tert-butyl-p-methyl-glycanal and 1.2 mmol of pentafluoroaniline synthesized according to the route of Example 1 were refluxed (90° C.) in absolute ethanol (50 mL) and reacted for 1 hour. Cool to room temperature and recrystallize with ethanol to obtain 6-tert-butyl-2((pentafluorophenylimino)-4-methylphenol with a yield of 92%, which is ready for use.

[0055] Under the protection of nitrogen, 50 mL of n-hexane was added to a dry Shrek bottle, and then 1.2 mmol of trichlorosilyl hydrogen was added to dissolve 1.0 mmol of 6-tert-butyl-2((pentafluorobenimino) in 25 mL of n-hexane )-4-Methylphenol and 1.1mmol of triethylamine were slowly added dropwise to the above system at 0°C, reacted for 1.5h, concentrated the solvent to 10mL, placed in a -20°C refrigerator for recrystallization, and obtained light yellow crystals , 3,4-benzyl, 2-oxa, 6-aza, 1,1-dichlorosilane compounds, the yield is 95%, and the structural formula is as follows:

[0056]

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Abstract

The invention discloses a hexahydroxy nitride oxide silicon heterocyclic compound and a preparation method thereof. The compound is shown as a formula (I); R1 is straight chain C1-C6 alkyls, C1-C5 alkyls with side chains or halogen-containing groups; R2 is straight chain C1-C5 alkyls, C1-C4 alkyls with side chains or substitutional straight chains or branched chain alkyls or halogen groups; Ar isC6-C10 aromatic groups or substitutional aromatic groups. The compound can be used as amidogen containing silicone oil and silicone rubber; preparation monomers of the heterocyclic compound with photoelectric performance have good application prospects. The invention also further discloses a method for preparing the heterocyclic compound in a formula (I) from a silane reduction Schiff base compound under the condition without catalysts. The reaction conditions are mild; the reaction time is short (smaller than 2h); the yield reaches 90 percent or above; the silane and imine reaction is enriched; a shortcut is provided for preparing the nitride oxide silicon heterocyclic compound through one-step method intramolecular cyclization reaction. (The formula (I) is shown in description.).

Description

technical field [0001] The invention relates to a six-membered nitrogen-oxygen-silicon heterocyclic compound and a preparation method thereof. Background technique [0002] Oxynitride silicon heterocyclic compounds have special photoelectric properties, and are also important monomers for the preparation of special nitrogen-containing silicone oils, silicone resins, and silicone rubbers. At present, silicon heterocompounds are mainly prepared by the dehydrochlorination reaction of chlorosilane and amine compounds. The reaction process is relatively violent, with many by-products, complex post-treatment, and the generated hydrogen chloride has a strong odor and strong corrosion to equipment. The reaction process is shown in formula a. Show. [0003] [0004] Using hydrogen-containing silane to react with imine structure compounds under the action of a metal catalyst, by activating the silicon-nitrogen double bond on the imine, the insertion of the silicon-hydrogen bond in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/02
CPCC07F7/025
Inventor 韩振刚韦清华徐人威王雄韩晓昱李艳芹穆蕊娟张鹏王海张平生
Owner PETROCHINA CO LTD
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